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Islip

$146+ Cheap flights from Chicago (CHI) to Islip, NY (ISP)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
Jun 24 — Jul 11
Wed 6/24
Wed 7/1
1 adult, Economy
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Find cheap flights from Chicago to Islip with Cheapflights

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2. Select your favorite providers

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3. Compare prices and book

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Cheap flight deals from Chicago to Islip

Cheapest flights from Chicago to Islip
Explore the most affordable flight options available from Chicago to Islip. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.

This Booking.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/244:59 pm
ORD
-
ISP
1 stop26h 58m
Frontier
Wed 7/19:52 pm
ISP
-
ORD
1 stop26h 27m
Frontier
Deal found 5/25$321
This Booking.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/224:59 pm
ORD
-
ISP
1 stop21h 57m
Frontier
Mon 6/299:52 pm
ISP
-
ORD
1 stop26h 27m
Frontier
Deal found 5/25$352
This CheapOair deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/134:59 pm
ORD
-
ISP
1 stop26h 58m
Frontier
Mon 6/159:52 pm
ISP
-
ORD
1 stop26h 27m
Frontier
Deal found 5/22$354
This Booking.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:30 pm
ORD
-
ISP
1 stop15h 33m
Frontier
Sat 8/2210:48 am
ISP
-
ORD
1 stop13h 26m
Frontier
Deal found 5/22$360
This Booking.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/174:59 pm
ORD
-
ISP
1 stop26h 58m
Frontier
Sat 6/209:52 pm
ISP
-
ORD
1 stop26h 27m
Frontier
Deal found 5/23$367
This Expedia deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/184:59 pm
ORD
-
ISP
1 stop26h 58m
Frontier
Sun 6/219:52 pm
ISP
-
ORD
1 stop12h 29m
Frontier
Deal found 5/20$368
This Expedia deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:13 pm
ORD
-
ISP
1 stop15h 40m
Multiple Airlines
Thu 7/304:58 pm
ISP
-
ORD
1 stop7h 46m
Multiple Airlines
Deal found 5/22$386
This Frontier deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1210:16 am
ORD
-
ISP
1 stop9h 41m
Frontier
Sun 6/149:52 pm
ISP
-
ORD
1 stop12h 29m
Frontier
Deal found 5/22$389
This CheapOair deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/124:59 pm
ORD
-
ISP
1 stop26h 58m
Frontier
Mon 6/159:52 pm
ISP
-
ORD
1 stop26h 27m
Frontier
Deal found 5/22$409
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:44 pm
ORD
-
ISP
1 stop15h 49m
Multiple Airlines
Sun 11/15:23 pm
ISP
-
ORD
2 stops23h 03m
Multiple Airlines
Deal found 5/23$419
This Frontier deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2610:16 am
ORD
-
ISP
1 stop9h 41m
Frontier
Sun 6/289:52 pm
ISP
-
ORD
1 stop12h 29m
Frontier
Deal found 5/21$430

Find flight deals from Chicago to Islip

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Islip (ISP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$321
(Booking.com)

One-way from

$146
(Booking.com)

Popular in

May

Cheapest in

January

Average price

$251
Provider with most accurate pricing for Chicago (CHI)-Islip Long Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Islip Long Island flights.
Search Deals
From Chicago (CHI) to Islip Long Island
Search Deals
One-way flight from Chicago (CHI) to Islip Long Island
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Islip that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 25, 2026.
Use the filters below to find and compare flights from Chicago to Islip that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 6/22

4:59 pm-3:56 pm

1 stop21h 57m

Islip Long Island

Mon 6/29

9:52 pm-11:19 pm

1 stop26h 27m

$352

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 6/17

4:59 pm-8:57 pm

1 stop26h 58m

Islip Long Island

Sat 6/20

9:52 pm-11:19 pm

1 stop26h 27m

$367

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 7/7

5:13 pm-9:53 am

1 stop15h 40m

Islip Long Island

Mon 7/13

2:28 pm-11:10 pm

2 stops33h 42m

$440

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 6/23

4:59 pm-8:57 pm

1 stop26h 58m

Islip Long Island

Sat 6/27

9:52 pm-11:19 pm

1 stop26h 27m

$441

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 6/12

10:16 am-8:57 pm

1 stop9h 41m

Islip Long Island

Tue 6/16

4:41 pm-11:19 pm

1 stop7h 38m

$449

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 6/19

10:16 am-8:57 pm

1 stop9h 41m

Islip Long Island

Mon 6/22

9:52 pm-5:07 am

2 stops32h 15m

$458

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 9/1

2:35 pm-10:56 pm

1 stop7h 21m

Islip Long Island

Wed 9/9

6:00 am-1:39 pm

1 stop8h 39m

$465
Quickest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 9/1

2:35 pm-10:56 pm

1 stop7h 21m

Islip Long Island

Tue 9/8

5:00 pm-11:44 pm

1 stop7h 44m

$465

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 9/1

2:35 pm-10:56 pm

1 stop7h 21m

Islip Long Island

Wed 9/2

6:00 am-1:39 pm

1 stop8h 39m

$465

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 9/1

2:35 pm-10:56 pm

1 stop7h 21m

Islip Long Island

Thu 9/10

6:00 am-1:39 pm

1 stop8h 39m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/24

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Chicago to Islip

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Islip in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Islip, New York flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Islip, New York flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Islip, New York flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Islip, New York flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Islip, New York flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Islip

Have a flexible travel schedule? Discover the best time to fly to Islip from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Islip
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Islip. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Islip from Chicago?

    Most people fly into Islip Long Island (ISP) if they book a flight to Islip from Chicago. On average, Long Island has 0 inbound flights from Chicago per day from 0 airlines. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

  • How long is the flight from Chicago to Islip, New York?

    There are many flights that can get you from Chicago to Islip, New York in 21h 57m. Fly via Frontier to get the fastest option. There are 770 mi between Chicago and Islip, New York.

  • Can I find deals for flights from Chicago to Islip that include hotel bookings?

    Yes. In addition to deals on Chicago to Islip flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Islip?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Islip.

  • Can I find deals for business class flights from Chicago to Islip?

    Yes. Cheapflights offers flight deals from Chicago to Islip by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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